The significant growth of the Caribbean community in the United States at the turn of the twentieth century is easily explained by the increasing economic hardship and disenchantment in the British West Indies and the simultaneous expansion of the U.S. economy with its relatively high wages and growing employment opportunities.

The British Caribbean experienced a catastrophic decline in its sugar industry. The British colonies found themselves unable to compete against cane sugar from Cuba and Brazil and against sugar beets produced in Europe. Between 1840 and 1900 the price of Jamaican sugar dropped almost 80 percent. The number of sugar estates on the island fell from 670 in 1836 to just 74 by 1910, drastically reducing the number of workers employed in the industry. Though banana cultivation expanded rapidly, it could never make up for the shortfall created by the collapse of the sugar economy.

Barbados's ruling class managed to break the fall of King Sugar on that island, but it did so on the backs of black Barbadians by instituting a mercilessly exploitative system. A similar dynamic enfolded in Saint Kitts, Nevis, Montserrat, and Antigua. The death rate, especially infant mortality, soared on these islands. Malnutrition was commonplace and outright starvation was not unknown. As one petitioner to the British government put it in 1899, "Her Majesty's black and colored subjects in the West Indies have had to choose between a death from starvation in their native islands and suffering ill-treatment as immigrants in the Dominican Republic because their native islands are merely Islands of Death."

The gravity of the situation was compounded by a series of natural disasters that contributed to emigration. Hurricanes, floods, and droughts afflicted the islands with unusual frequency and intensity between 1880 and 1920. The structure and oppressiveness of colonial rule on the islands took its toll not only on the workers and peasants but also on the aspiring black middle class. They became increasingly dissatisfied. Black teachers received meager salaries and no pensions at the end of their careers. Those few who made it into the civil service were locked down in low-level jobs,
well below their capabilities. To make matters worse, in 1911 the Jamaican authorities decided to scrap competitive civil service examinations. They were replaced by an undemocratic appointment system that favored the whites and the light-skinned. There were strong and loud objections, but they were ignored.